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Sleepy Hollow, New York Homes for Sale

The historic Village of Sleepy Hollow is located on the eastern shore of the Hudson River, 25 miles north of Manhattan. With a population of about 9,000, Sleepy Hollow is home to a diverse and vibrant community that includes a large number of professionals who make the easy forty-minute commute by train into Manhattan.

Today Sleepy Hollow combines city convenience and small-town charm. Residents enjoy a plethora of outdoor adventures with parks, forests, rivers, lakes, streams and trails along one of the most scenic stretches of the Hudson River.

Beautiful Sleepy Hollow is home to a very wide range of different housing types and styles, starting with coop and condo developments in the low 100,000's and up, through single family homes in all price ranges, and ending with multi-million-dollar mansions and estates. Many of these homes are perched atop the hills overlooking the Hudson River Valley and surrounding landscape. In addition Sleepy Hollow is currently in the planning stages to rebuild its waterfront within a comprehensive master site plan including town homes, stores, professional spaces, restaurants, public ball fields and parks. Part of it, GDC's Ichabod's Landing community of townhouses, is already completed.

Immortalized in Washington Irving’s famous tale, The Legend of Sleepy Hollow, this quiet Village has preserved much of its history and natural beauty. Initially an agricultural district, Sleepy Hollow later became a manufacturing center, producing items such as steam-powered automobiles, shoes, and batteries. Around the turn-of-the-century, Sleepy Hollow's bucolic setting and close proximity to Manhattan attracted millionaires like Anson Phelps, Ambrose Kingsland and John D. Rockefeller, who built beautiful mansions in the area, some of which are open to the public. Tarrytown also boasts several world famous landmarks including Philipsburg Manor, the Old Dutch Church and the Rockefeller Family Estate Kykuit.

Sleepy Hollow shares its public school system with its close neighbor Tarrytown. The Public Schools of the Tarrytowns stretch along the east bank of the Hudson River, serving students from the villages of Sleepy Hollow and Tarrytown. It is an ethnically and socio-economically diverse district. The mission of the Public Schools of the Tarrytowns is to empower students to make informed choices and assume responsibility for their own actions as they become self-directed, lifelong learners who are committed and able contributors to a sustainable local and global society. 

Village of Sleepy Hollow: http://www.sleepyhollowny.gov
Public Schools of the Tarrytowns: http://www.tufsd.org

Sleepy Hollow Homes for Sale

$12,000,000
5 Beds ⋅ 6 Baths ⋅ H6335041 MLS
Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central core is a great room with 20 foot ceilings and walls of glass facing the river. Equestrian facilities include a 14-stall stable, indoor and outdoor riding arenas, six fenced paddocks and two grooms's apartments. A manager's house, greenhouse, carriage barn and equipment garage are all well located to support the stable, main house and property. Direct trail access from the property is provided through north and south gates to the 55-mile carriage trail network of the 1,800 acre Rockefeller State Park. Winterburn Farm is an extremely rare opportunity offering a pristine architectural house amid a beautiful landscape of unparalleled privacy.

48 Raafenberg Road, Sleepy Hollow
$3,995,000
3 Beds ⋅ 4 Baths ⋅ 968348 MLS
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting. Our uncompromising commitment to quality extends into each uniquely designed residence with spacious open floor plans and crafted, quality materials. Fully-equipped kitchens offer state-of-the-art integrated appliances while bathrooms offer a private oasis clad in marble with floating tubs. The Daymark lifestyle extends beyond each residence with indoor/outdoor amenities including lobby with concierge, fitness center with yoga studio and swimming pool with stunning views. The indoor and outdoor amenity spaces have been thoughtfully curated to support life, work and a passion for healthy, balanced living. Additional Information: Amenities:Storage,

4 Lighthouse Landing Unit #204, Sleepy Hollow
$3,895,000
3 Beds ⋅ 4 Baths ⋅ 924705 MLS
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting. Our uncompromising commitment to quality extends into each uniquely designed residence with spacious open floor plans and crafted, quality materials. Fully-equipped kitchens offer state-of-the-art integrated appliances while bathrooms offer a private oasis clad in marble with floating tubs. The Daymark lifestyle extends beyond each residence with indoor/outdoor amenities including lobby with concierge, fitness center with yoga studio and swimming pool with stunning views. The indoor and outdoor amenity spaces have been thoughtfully curated to support life, work and a passion for healthy, balanced living. Additional Information: Amenities:Storage,

4 Lighthouse Landing Unit #210, Sleepy Hollow
$3,115,000
3 Beds ⋅ 3 Baths ⋅ 979271 MLS
Priced To Sell! Welcome to The Daymark Condominium at Sleepy Hollow, a luxurious residence marked by stunning expansive waterfront views, abundant natural light, and a lifestyle of grand distinction. This brand new and never occupied 3-bedroom, 2.5 bath uniquely designed residence of unparalleled excellence, is available for immediate occupancy! As to what distinguishes this residence - 2 parking spaces with EV charging and an optional private locked storage facility conveniently located on the same floor available to purchase. Upon entering The Daymark, you will be drawn to the soaring two-story wood paneled lobby/reception area with its dramatic staircase, bespoke concierge desk, lobby lounge, mail, cart, and package rooms. Upon entering this ideal corner residence, herringbone floor accents define the foyer, and wide-plank white oak flooring throughout the open floorplan offers a neutral and serene foundation to custom design your space. Spacious sunlit rooms showcase large picture windows and 9+ft high ceilings provide sweeping views of the Hudson River, NY City Skyline, Riverwalk, waterfront park, and M. Cuomo Bridge that will take your breath away. The corner loggia situated off the kitchen bridges the indoor and outdoor spaces providing unobstructed views of the Hudson and beyond. The elegantly designed gourmet kitchen features organic color tones and textures utilizing custom oak cabinetry with scalloped details, quartz counter tops, Subzero-Wolf appliances, gas cooktop and oven, integrated wine refrigerator, integrated microwave, dishwasher, and garbage disposal. The individualized bathrooms highlight marble tiles, oak millwork, custom fixtures and lighting. The primary bathroom is accentuated in marble and walnut with mosaic radiant heated floors, and floating tub. Some of the many distinguishing features and amenities of the Daymark include: A luxurious pool with waterfront views nestled on a landscaped terrace with hot tub and fire pit, sauna, shower and changing room. Fitness center, yoga studio, library with fireplace, Hudson Club, bar lounge, conference room, study, children's playroom, coffee bar, tea bar, courtyard lounge, landscaped rooftop lounge with observation terrace, outdoor kitchen/grill/barbecues. Conveniently located within walking distance to both the Tarrytown and Philipse Metro-North stations with just under a 40-minute commute to Grand Central. DeCicco supermarket, restaurants, boat docking/fishing pier, kayak launch, park, and more either exist or soon to come. The calm and beauty of the Riverwalk pathway is yours to enjoy just steps from your residence. The Daymark is truly a one-of-a-kind lifestyle experience!

4 Lighthouse Landing Unit #424, Sleepy Hollow
$2,620,000
3 Beds ⋅ 5 Baths ⋅ 811522 MLS
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting. Our uncompromising commitment to quality extends into each uniquely designed residence with spacious open floor plans and crafted, quality materials. Fully-equipped kitchens offer state-of-the-art integrated appliances while bathrooms offer a private oasis clad in marble with floating tubs. The Daymark lifestyle extends beyond each residence with indoor/outdoor amenities including lobby with concierge, fitness center with yoga studio and swimming pool with stunning views. The indoor and outdoor amenity spaces have been thoughtfully curated to support life, work and a passion for healthy, balanced living. Additional Information: Amenities:Storage,

4 Lighthouse Landing Unit #TH14, Sleepy Hollow
$2,500,000
4 Beds ⋅ 5 Baths ⋅ 1007046 MLS
The Layout and First Impressions Living in this modern, four-level end-unit brownstone is an absolute dream. The home is completely flooded with natural light, which perfectly highlights the neutral color palette. No expenses were spared on upgrades, putting down top-tier Light Oak engineered hardwood throughout the entire home. When you enter on the ground floor, you walk into a functional space featuring a mudroom, direct access to the two-car garage, and a flexible bedroom that can be used as a home office. Main Living and Gourmet Kitchen Upstairs is the heart of the home—an open-layout living with high-end finishes. The kitchen is a true chef’s space with crisp white cabinetry, top of the line appliances, a massive center (extra thick) marble island, and endless counter space. In the living room, the absolute focal point is the floor-to-ceiling dark stone fireplace surround, which naturally draws people in for conversation. The dining room feels straight out of a design magazine, anchored by a glamorous, custom breakfront that always sets an elegant tone for dinner parties. Note: All four of the Bedrooms have ensuite bathrooms. The primary suite on the third floor is a personal sanctuary. It features two massive walk-in closets and a spectacular, tres chic spa bath with specifically chosen fixtures. The laundry room is conveniently located on this same floor, right next to the second bedroom. On the top floor, a built out a fully finished loft. It has a third bedroom that is perfect for guests or a second home office. It also features a 15-foot square den equipped with its own refrigerator, sink, & dishwasher creating a Wet Bar area—ideal for watching the game and/or entertaining in general. Best of all the rooftop terrace is where you can enjoy daytime sun or spend your evenings, taking in breathtaking views of the waterfront and the bridge. The partially covered terrace (which also allows you to have the option to escape the sun if/when desired) is equipped with a custom outdoor kitchen with a built-in grill. There is also a natural gas fireplace (which is a rare amenity sighting in these style brownstones) making it an incredible & unique spot for alfresco outdoor dining and hosting. The location itself is unbeatable. Just steps from the front door is the RiverWalk paths featuring gorgeous landscaping, benches, nighttime lighting, performance spaces, and Horan's Landing Park giving access to paddleboarding & Kayaking. Let's not leave out the Historic Lighthouse flanked by Kingsland Point Park. To make things even sweeter, the new DeCicco's market is just a stones throw away. Amazing list of extra amenities included: This "High-Tech" unit is equipped with automatic blackout shades throughout if/when desired. Actually...you will be able to control the thermostat, blinds, tv's, and speakers all from your smartphone (via: Control4 Ring, & MyQ programs/apps. It provides a quick 37-minute commute to Manhattan and sits steps from the historic, amenity-rich village of Sleepy Hollow & Tarrytown.

324 Horseman Boulevard, Sleepy Hollow
$2,175,000
4 Beds ⋅ 5 Baths ⋅ 1010732 MLS
Introducing one of the most exceptional residences in the sought-after Edge-on-Hudson. This stunning Toll Brothers end-unit, the largest model in the community, has been extensively upgraded and professionally designed, offering a level of sophistication and customization rarely found in new construction. Walls of windows and glass doors bathe the home in natural light, creating bright, inviting spaces and seamless indoor-outdoor living. Thoughtfully curated by a professional interior designer, the residence showcases elevated finishes, custom details, and a refined aesthetic throughout. The spectacular rooftop retreat serves as a private oasis, featuring a covered outdoor living room with lounge seating and an expansive open-air terrace ideal for dining, entertaining, and relaxing. Equally impressive is the custom-finished two-car garage, designed to complement the home’s luxury lifestyle while providing exceptional functionality and storage. Combining the privacy and abundance of light afforded by a premier end location with extensive upgrades, designer finishes, and outstanding indoor and outdoor living spaces, this turnkey residence represents a rare opportunity within Westchester’s premier waterfront community. Conveniently located On the Hudson River, The Riverwalk, parks, restaurants, shopping, and Metro-North for an effortless short commute to Manhattan.

340 Horseman Boulevard, Sleepy Hollow
$1,950,000
4 Beds ⋅ 5 Baths ⋅ 1005652 MLS
Experience the pinnacle of waterfront living in this extraordinary Park Model residence, the largest and most extensively customized townhome in the prestigious Edge-on-Hudson Brownstone collection. Perfectly positioned to capture sweeping Hudson River vistas and the glowing lights of the Mario M. Cuomo Bridge, this exceptional home transcends standard luxury through bespoke craftsmanship, designer finishes, and state-of-the-art infrastructure. The journey begins on the entry level with a sophisticated library-style study, or first-floor bedroom, featuring herringbone flooring and a hand-carved sandstone mantel on a decorative fireplace meticulously crafted by artisans in India. This level of thoughtful design continues throughout the residence, from the designer wallpapered “jewel box” powder rooms to the custom millwork, curated finishes, and three distinctive gas fireplaces that create warmth and character across multiple living spaces. At the heart of the home is a world-class chef’s kitchen designed for both everyday living and elegant entertaining. Anchored by an oversized waterfall concrete island, the space features furniture-quality custom cabinetry and a professional-grade appliance suite including Wolf, Sub-Zero, and Miele. The kitchen flows seamlessly into the expansive Great Room, where a stunning custom marble gas fireplace serves as a dramatic focal point, framed by elegant architectural detailing and abundant natural light. Upstairs, the primary suite offers a boutique-hotel-inspired sanctuary with dual walk-in closets and a spa-like bath featuring a freestanding soaking tub, and custom designer mirrors. Additional guest accommodations provide flexibility for family and visitors, while a dedicated laundry room conveniently located on the bedroom level offers exceptional everyday convenience. The top floor functions as a private retreat, an en-suite bedroom and bath, complete with its own gas fireplace. From here, French doors open onto a truly spectacular rooftop oasis with stunning river views designed for year-round entertaining. This remarkable outdoor living space features an automated louvered pergola, premium wood decking with integrated lighting, a built-in Alfresco outdoor kitchen, under counter refrigeration, and a gas fireplace for cooler evenings—all set against panoramic Hudson River views that create an unforgettable backdrop for dining, entertaining, or simply watching the sunset or fireworks. The lifestyle here is defined by effortless connection and exceptional convenience. Whether starting your morning on the scenic riverfront paths, picking up gourmet essentials at DeCicco & Sons, enjoying waterfront parks and green spaces, or taking the private shuttle to Metro-North for a seamless Manhattan commute, every amenity is at your doorstep. Residents also enjoy premier access to the Tarrytown Recreation Center, featuring a swimming pool, fitness center, tennis courts, and pickleball facilities. This is far more than a residence—it is a sophisticated waterfront sanctuary designed for those who refuse to compromise on quality, craftsmanship, lifestyle, or location.

207 Palisades Boulevard, Sleepy Hollow
$1,850,000
4 Beds ⋅ 5 Baths ⋅ 971740 MLS
Please send pof or pre app to phyllis before showing...Beautiful 4-bedroom, 3 full and 2 half bath townhome at Brownstone- Edge on Hudson, perfectly positioned to capture breathtaking river views and the iconic Mario Cuomo Bridge. This exceptional home showcases top-notch craftsmanship in the heart of Sleepy Hollow along the Hudson River. Designed for today’s modern lifestyle, it features an open floor plan, high ceilings, oversized windows, and rich hardwood floors throughout. The first level offers a flexible bedroom or home office with a full bath, a mudroom, and direct access to the two-car garage. On the second floor, natural light pours into the spacious dining area, gourmet kitchen is a chef's dream, complete with high-end appliances a walk-in pantry, and oversize center island. Living room, which features a gas fireplace, custom built-ins, and access to a private terrace. A powder room completes this level. Upstairs, the primary suite offers a walk-in closet and a luxurious en-suite bath. Two additional bedrooms, hall bath and laundry . The top level is designed for entertaining, featuring a large recreation room with a half bath, wine fridge, ice maker, and projector with screen. Step outside to a loft-style area with a counter, sink, and dishwasher, leading to a spacious deck with stunning river and bridge views. Enjoy a vibrant waterfront lifestyle with a scenic river walk and the nearby upscale DeCicco & Sons gourmet market, offering a specialty deli, fresh baked goods, a bar, and a large outdoor patio. Convenient jitney service to Tarrytown and easy access to Metro-North provide a seamless commute to Manhattan. This exceptional location combines the charm of picturesque villages, historic landmarks, and expansive green space with modern convenience. Don’t miss this one!

203 Palisades Boulevard, Sleepy Hollow
$1,840,000
2 Beds ⋅ 3 Baths ⋅ 1027122 MLS
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting. Our uncompromising commitment to quality extends into each uniquely designed residence with spacious open floor plans and crafted, quality materials. Fully-equipped kitchens offer state-of-the-art integrated appliances while bathrooms offer a private oasis clad in marble with floating tubs. The Daymark lifestyle extends beyond each residence with indoor/outdoor amenities including lobby with concierge, fitness center with yoga studio and swimming pool with stunning views. The indoor and outdoor amenity spaces have been thoughtfully curated to support life, work and a passion for healthy, balanced living. Additional Information: Amenities:Storage,

4 Lighthouse Landing Unit #305, Sleepy Hollow
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